Fluoroolefins represented by the formula: CF3(CX2)nCF═CH2, the formula: CF3(CX2)nCH═CHF (wherein n is an integer of 1 or more, and X is a halogen atom, such as fluorine or chlorine), or the like, are used for various applications, such as functional materials, solvents, refrigerants, and foaming agents. Further, these fluoroolefins are known to be compounds that have a useful structure as monomers or raw materials for producing functional polymers. For example, they are used as monomers for modifying ethylene-tetrafluoroethylene copolymers. Thus, these fluoroolefins are used for various applications and as various raw materials, and are highly useful compounds. Of these fluoroolefins, a compound represented by CF3CF═CH2 (HFO-1234yf) and a compound represented by CF3CH═CHF (HFO-1234ze) show increasing promise as refrigerant compounds with a low global-warming potential.
A fluoroolefin represented by an aforementioned formula is reportedly produced by, for example, reacting a chlorine-containing alkane or chlorine-containing alkene having the same number of carbon atoms, which is used as a starting material, with a fluorinating agent, such anhydrous hydrogen fluoride, in the presence of a catalyst (see PTL 1, mentioned below).
Moreover, of the fluoroolefins represented by the above formulas, HFO-1234yf is known to be produced by continuous vapor phase fluorination reaction of a chlorine-containing olefin, such as CF3CCl═CH2 (HCFO-1233xf), in the presence of a catalyst. HFO-1234yf produced in this manner has particularly attracted attention as a refrigerant with a low global-warming potential.
Furthermore, of the fluoroolefins represented by the above formulas, HFO-1234ze is known to be produced by continuous vapor phase fluorination reaction of a chlorine-containing olefin, such as CF3CH═CHCl (HCFO-1233zd), in the presence of a catalyst. For example, PTL 2 discloses that HFO-1234ze is produced by reacting HCFO-1233zd with hydrogen fluoride in the presence of a copper/chromium catalyst.